Following up on my own post:
Did not get to visit Guadalupe from Trujillo. It would have not been possible without spending the night. Perhaps in the summer season this would have been possible but not the end of September. I noticed alot of the schedules in Extremadura switched in mid September.
Another important note for people using public transporation to Trujillo. I've been all over Spain and this was a first: Arrived at the bus station in the early evening (6 pm) in Trujillo and there were no taxis in sight. Tried to contact a taxi from the phone numbers for taxis at the pay phone in the bus station bar but no one answered. Finally called the parador (where I was staying), told them my predicament, and with their assistance got a taxi after another 30 minutes. Apparently, Trujillo only has 3 taxis in town and one was broken down. On my return to the bus station, I requested the parador to call ahead an hour before I wanted to leave but they couldn't reach a taxi until the last minute and I almost missed my bus. It seems that one of the two working taxis took some travelers to Caceres so the whole town only had one taxi. Ironically, I met a lady at the bus station who was traveling with her elderly mother and they had to have someone from their hotel give them a ride to the bus station because they couldn't find a cab.
I guess this is what makes the trip adventurous though!